Process for preparing a new tetralin derivative



Patented Mar. 21, 1939 PROCESS FOR PREPARING A NEW TETRALIN DERIVATIVEYasuhiko Asahina, Tokyo, Japan N Drawing. Application March 12, 1938,Serial No. 195,656. In Japan June '7, 1937 2 Claims.

This invention relates to a process for preparing a new tetralinderivative and its object is to obtain a new substance which has ananthelmintic effect.

is extracted with ether.

This ether solution is The process of this invention consists ofobshaken with 100 cc. of 5% sulfuric acid, whereby 5 taining first6-hydroxylamino-tetralin by reducthe substance is now transferred intothe acid ing G-nitroltetralin and of subsequently treating solution. Theacid solution is heated on a waterthe product with a dilute mineral acidto produce bath for 5 to 10 minutes and is extracted withtetralylquinol, a new substance, which has a ether after cooling. stronganthelmintic effect. The heating and extraction with new ether are 10fi-hydroxylamino-tetralin is made from 6-nirepeated several times. Theether extracts thus trotetralin by an ordinary method of reduction,obtained are all united and condensed by evaporafor instance, reductionof a solution of tetralin tion. Upon the addition of petroleum-ether toin either ethanol or methanol or other alcohols the condensed etherextract a crystalline precipiby a mixture of zinc and a chloride ofeither amtate is obtained, which is subjected to re-crystalmonium orcalcium or barium. Reduction by lization using ether. The yield is 0.4gram. either ammonium amalgam or ammonium sulfide Exam Z6 2 or byelectrolytic process is also used for the purp pose (Journal fijrpraktische Ch i N 5 grams of fi-nitrotetralin dissolved in 50 cc. Folge,Bd. 142,167). ethanol is reduced in the cold with ammonium The product,6-hydroxylamino-tetralin, is then amalgam Which has been Obtained y eosubjected to Bambergers reaction by using a lyzing o u Sulfate Withmercury Cathodemineral acid so that tetralylquinol is obtained. Thereduction p Y 0- etra n,

Thi ub t ha t b reported far i is treated in the same manner asdescribed in the any literature. It is a prismatic crystal and itsexample 1, thus tetralylquinol being Obta ned- 5 melting point is 124C.-l C. The y d is gram.

It is an effective anthelmintic' and acts directly What I Claim uponascarisand other nematodes 1. A process of preparing a tetralinderivative The aforementioned chemical reactions may possessinganthelmintie effect, Which o p ses be represented by the followingchemical scheme: fi 1 scinitretetlalin Hi l zi y lu ml t f ate rain anconver ing e a er 0 e ra y H0HI\\ O\ quinol by treatment with a mineralacid.

[L/ acid Tetralylquinol, corresponding to the forreduction treatment Ina: V 29 Example 1 5 grams of fi-nitrotetralin is dissolved in 25 cc. of85% ethanol and 0.5 gram to 1.0 gram of H chloride of either ammonium orcalciumv or barand being a tetralin derivative with anthelmintic ium isadded thereto. After the addition of 5 grams to'6 grams of zinc powder,the mixture is effect.

YASUHIKO ASAHINA.

